(R)-methyl 2-((4R,5R)-5-(hex-5-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate | 1446403-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-methyl 2-((4R,5R)-5-(hex-5-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate
• 英文别名: methyl (2R)-2-[(4R,5R)-5-hex-5-enyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
• CAS: 1446403-77-5
• 化学式: C₁₄H₂₄O₅
• 分子量: 272.342
• InChiKey: GTYUPDBZXLNJHW-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-((4R,5R)-5-(hex-5-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate 在 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.34h， 生成 (S)-methyl 2-((4R,5R)-5-(hex-5-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate
  参考文献：
  名称：

  Enantiospecific formal total synthesis of (+)-aspicilin

  摘要：

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.041
• 作为产物：
  描述：

  magnesium,hex-1-ene,bromide 在 cerium(III) chloride heptahydrate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 4.0h， 生成 (R)-methyl 2-((4R,5R)-5-(hex-5-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate
  参考文献：
  名称：

  Enantiospecific formal total synthesis of (+)-aspicilin

  摘要：

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.041

文献信息

• Enantiospecific formal total synthesis of (+)-aspicilin
  作者：Vasudeva Rao Gandi

  DOI：10.1016/j.tet.2013.05.041

  日期：2013.8

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.